With the fall of the Taliban in 2001 and their return in 2021, Afghanistan has undergone drastic socio-political changes. In many families, children are introduced to the practice of “Bacha Posh” (dressing up like a boy), an Afghan cultural custom where girls are dressed up as boys until they are married off. Despite children being central to this practice, it has not been studied through their eyes. This article examines the custom of Bacha Posh through the children’s perspective and situates it within the current socio-political scenario of the country. A textual and cultural analysis of three literary works is carried out through a study of their child characters to examine how Afghan culture creates its own gender construct. Two are significant works of children’s literature that revolve around real-life stories of Bacha Posh – Nadia Hashimi’s One Half from the East (2016) and Deborah Ellis’ The Breadwinner (2000). The third work is The Underground Girls of Kabul (2014) by Jenny Nordberg, a seminal work in the study of Bacha Posh in which Nordberg focuses on the practice of Bacha Posh and presents the voice of children. This article then goes on to study the impact of the restrictive nature of the Taliban regime on girls and its influence on the cultural custom of Bacha Posh. It demonstrates how this practice creates an unstable gender construct among children, as evidenced by the gender dysphoria that some girls experience. It thus demonstrates the impact of culture on gender through filling in the gaps between culture, literature and politics.